Compound, rubber blend containing the compound, vehicle tire comprising the rubber blend in at least one component, process for producing the compound, and use of the compound as an ageing protectant and/or antiozonant and/or dye

Abstract

A compound, a rubber mixture containing the compound, a vehicle tire comprising the rubber mixture in at least one component, a process for producing the compound and the use of the compound as an aging stabilizer and/or antiozonant and/or dye, in which, the compound has the formula (I), wherein R 1 is selected from the group consisting of benzyl radicals, 1-phenylalkyl radicals having altogether 7 to 18 carbon atoms and linear, branched and cyclic aliphatic C 3 - to C 12 -radicals.

1 .- 15 . (canceled) 
     
     
         16 . A compound of formula I): 
       
         
           
           
               
               
           
         
         wherein R 1  is selected from the group consisting of benzyl radicals, 1-phenylalkyl radicals having altogether 7 to 18 carbon atoms and linear, branched and cyclic aliphatic C 3 - to C 12 -radicals, and 
         wherein R 3  is selected from the group consisting of linear, branched and cyclic aliphatic C 1 - to C 12 -radicals, and aryl radicals, cyano radicals, halogen radicals, ether radicals and thioether radicals, and wherein n assumes the value 0 or 1 or 2 or 3 or 4, wherein when n is 2 or 3 or 4 the radicals R 3  are independently of one another identical or different, and 
         wherein R 2  is selected from the group consisting of linear, branched and cyclic aliphatic C 1 - to C 12 -radicals, and aryl radicals, cyano radicals, halogen radicals, ether radicals and thioether radicals, and 
         wherein m assumes the value 0 or 1 or 2 or 3, wherein when m is 2 or 3 the radicals R 2  are independently of one another identical or different. 
       
     
     
         17 . The compound as claimed in  claim 16 , wherein n is 0 (zero). 
     
     
         18 . The compound as claimed in  claim 16 , wherein m is 0 (zero). 
     
     
         19 . The compound as claimed in  claim 16 , wherein R 1  is bonded to the nitrogen atom (N) via a tertiary carbon atom. 
     
     
         20 . The compound as claimed in  claim 16 , wherein R 1  is a branched alkyl radical having 3 to 12 carbon atoms, or a 1-phenylalkyl radical having altogether 7 to 10 carbon atoms. 
     
     
         21 . The compound as claimed in  claim 20 , wherein the branched alkyl radical has 4 to 8 carbon atoms. 
     
     
         22 . The compound as claimed in  claim 16 , wherein R 1  is selected from the group consisting of 1,3-dimethylbutyl, 1-phenylethyl and cyclohexyl radicals, 
     
     
         23 . The compound as claimed in  claim 16 , wherein R 1  is a 1,3-dimethylbutyl radical. 
     
     
         24 . The compound as claimed in  claim 16 , wherein the halogen radicals include fluorine, bromine or chlorine radicals. 
     
     
         25 . The compound as claimed in  claim 16 , wherein the compound has the structure of formula II): 
       
         
           
           
               
               
           
         
       
     
     
         26 . A method of using the compound as claimed in  claim 16 , comprising:
 providing the compound, and   using the compound as an aging stabilizer in a vehicle tire and/or a technical rubber article and/or oil and/or lubricant.   
     
     
         27 . The method of  claim 26 , wherein the technical rubber article is an air spring, bellows, conveyor belt, belt, drive belt, hose, rubber band, profile, a seal, a membrane, tactile sensors for medical applications or robotics applications, or a shoe sole or parts thereof. 
     
     
         28 . A method of using the compound of  claim 16 , comprising:
 providing the compound,   using the compound as a dye in fibers and/or polymers and/or paper and/or in paints and/or coatings.   
     
     
         29 . A process for producing the compound of formula I) which comprises the following process steps:
 a1) providing the compound of formula A1)   
       
         
           
           
               
               
           
         
         b1) reacting the compound of formula A1) with a base, in particular potassium carbonate (K 2 CO 3 ), to obtain the compound of formula B1): 
       
       
         
           
           
               
               
           
         
         c1) reacting the compound of formula B1) with hydrogen or a hydrogenating reagent, and a ketone or aldehyde, to afford the compound of formula I): 
       
       
         
           
           
               
               
           
         
         wherein R 1  is selected from the group consisting of benzyl radicals, 1-phenylalkyl radicals having altogether 7 to 18 carbon atoms and linear, branched and cyclic aliphatic C 3 - to C 12 -radicals, and 
         wherein R 3  is selected from the group consisting of linear, branched and cyclic aliphatic C 1 - to C 12 -radicals, and aryl radicals, cyano radicals, halogen radicals, ether radicals and thioether radicals, and wherein n assumes the value 0 or 1 or 2 or 3 or 4, wherein when n is 2 or 3 or 4 the radicals R 3  are independently of one another identical or different, and 
         wherein R 2  is selected from the group consisting of linear, branched and cyclic aliphatic C 1 - to C 12 -radicals, and aryl radicals, cyano radicals, halogen radicals, ether radicals and thioether radicals, and 
         wherein m assumes the value 0 or 1 or 2 or 3, wherein when m is 2 or 3 the radicals R 2  are independently of one another identical or different, 
         and wherein X is a halogen, in particular fluorine (F), chlorine (Cl) or bromine (Br). 
       
     
     
         30 . The process as claimed in  claim 29 , wherein the reaction in step c1) with hydrogen and the aldehyde or ketone is carried out using a hydrogenation catalyst and at a temperature of 120° C. to 150° C. and the reaction mixture is subjected to hydrogen at a pressure of 35 to 45 bar and the reaction is carried out in an autoclave or in another pressure reactor. 
     
     
         31 . A process for producing the compound of formula I) which comprises at least the following process steps:
 a2) providing a compound of formula A2):   
       
         
           
           
               
               
           
         
         and 
         b2) providing a compound of formula B2): 
       
       
         
           
           
               
               
           
         
         and 
         c2) reacting the compound of formula A2) with the compound of formula B2) in the present of a halogenating agent such as PCl 3 , POCl 3 , PBr 3  or SOCl 2  to afford the compound of formula C2): 
       
       
         
           
           
               
               
           
         
         and 
         d2) reacting the compound of formula C2) in the presence of an acid, such as in particular acetic acid, to afford the compound of formula B1): 
       
       
         
           
           
               
               
           
         
         and 
         e2) reacting the compound of formula B1) with hydrogen or a hydrogenating agent and a ketone or aldehyde to afford the compound of formula I): 
       
       
         
           
           
               
               
           
         
         wherein R 1  is selected from the group consisting of benzyl radicals, 1-phenylalkyl radicals having altogether 7 to 18 carbon atoms and linear, branched and cyclic aliphatic C 3 - to C 12 -radicals, and 
         wherein R 3  is selected from the group consisting of linear, branched and cyclic aliphatic C 1 - to C 12 -radicals, and aryl radicals, cyano radicals, halogen radicals, ether radicals and thioether radicals, and wherein n assumes the value 0 or 1 or 2 or 3 or 4, wherein when n is 2 or 3 or 4 the radicals R 3  are independently of one another identical or different, and 
         wherein R 2  is selected from the group consisting of linear, branched and cyclic aliphatic C 1 - to C 12 -radicals, and aryl radicals, cyano radicals, halogen radicals, ether radicals and thioether radicals, and 
         wherein m assumes the value 0 or 1 or 2 or 3, wherein when m is 2 or 3 the radicals R 2  are independently of one another identical or different, 
         and wherein X is a halogen, in particular fluorine (F), chlorine (Cl) or bromine (Br). 
       
     
     
         32 . The process as claimed in  claim 31 , wherein the reaction in step e2) with hydrogen and the aldehyde or ketone is carried out using a hydrogenation catalyst and at a temperature of 50° C. to 70° C. and the reaction mixture is subjected to hydrogen at a pressure of 15 to 25 bar and the reaction is carried out in an autoclave or in another pressure reactor. 
     
     
         33 . A rubber mixture containing the compound as claimed in  claim 16 , wherein the rubber mixture contains at least one diene rubber which is selected from the group consisting of natural polyisoprene (NR rubber), synthetic polyisoprene (IR), butadiene rubber (BR), solution-polymerized styrene-butadiene rubber (SSBR), emulsion-polymerized styrene-butadiene rubber (ESBR), butyl rubber (IIR) and halobutyl rubber. 
     
     
         34 . A vehicle tire comprising the rubber mixture as claimed in  claim 33  in at least one component. 
     
     
         35 . The vehicle tire of  claim 34 , wherein the at least one component is at least one outer component, wherein the at least one outer component is a tread, a sidewall and/or a flange profile.